Table 1 Optimization of the reaction parameters

From: Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C−C cleavage and ruthenium-catalysed remote C−H activation

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Entry

Variation from the standard conditionsa

Yield (%)b

1

None

75

2

PPh3/P[3,5-(CF3)2C6H3]3/P(4-OMeC6H4)3

54/34/43

3

bpy/NHC as ligandc

0/trace

4

[Ru(OAc)2(p-cymene)]/[RuCl2(p-cymene)]2

52/5

5

[Ru(tBuCN)5(H2O)](BF4)2

21d/ 30

6

No catalyst/no ligand

0/0

  1. aReaction conditions: 1a (0.3 mmol), 2a (3.0 equiv.), 3a (3.0 equiv.), [Ru] (10 mol%), ligand (10 mol%), Na2CO3 (2.0 equiv.), 1,4-dioxane (2.0 ml), T = 65 °C, t = 24 h.
  2. bYield of isolated products.
  3. cbpy, 2,2′-bipyridine, NHC ligand used 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride.
  4. dT = 50 °C.
  5. Ac, acetyl; Bn, benzyl; Mes, mesityl; 2-Py, 2-pyridyl.
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